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7 tips for freelancing, working at home + being your own boss

January 22, 2014

Last year was the first year of my freelance career. It was shaky, unsure and I rarely saw the light at the end of the tunnel. But what was perhaps even harder was figuring out how to successfully work from home. Can I wear yoga pants? Is it awful to sleep in? Is it weird to take the morning off and work at night?

Over the course of a year I’ve figured out a few things about what works for me (dressing up — maybe not in sequin leggings) and what doesn’t (heavy lunches), but I still have my fair share to learn. So I turned to three fabulous freelancer friends who are imparting their words of wisdom on what it’s like to be an at-home worker bee. Read on for their thoughts on sleeping in, separating work from home and watching Bravo.

On giving in to naps, TV, etc.The secret to staying on track is to not view naps/TV/vegging on the couch as “bad” things, but simply as activities to enjoy in moderation. I would be lying if I said I didn’t take mini breaks throughout the day to catch up on Bravo reality shows or to lay down for a little bit for a mid-afternoon refresher! I find that the best part about working for myself is that I am the only person in charge of my schedule. If the couch is calling to me, I give it my attention for thirty minutes and then I return to work and never feel deprived. Always allow yourself a little bit of wiggle room!

On guilty feelings when you sleep in or go out to breakfast…
This is something I struggle with EVERY. SINGLE. DAY. While most of the world has to get up early and punch the clock from 9-5, I don’t have anyone making sure that I get up on time, get dressed, and accomplish all of my work between certain hours in order to get paid…that’s all on me. While this is the greatest gift EVER (I truly believe it!), it also makes me feel like I constantly have to “prove” to others that I really am working!

My advice for those particularly guilty moments is to reevaluate your current situation and ask yourself: “What are the immediate and long term consequences that I will have to face if I take a day off / sleep in / etc?” Usually, the answers will show that there are very few detriments to treating yourself to a little break from work. In fact, I find that taking a break from my routine actually helps me to be more productive and inspired when I return to work! You can’t possibly expect yourself to work 24/7. After all, what’s the point of freelancing if you never feel free?

On dressing up for work at home…
I actually enjoy having a clean face and working in my comfy clothes! Hey, that’s one of the upsides of working for yourself, right? If this doesn’t work for you, perhaps schedule a coffee date in the morning that way you come home feeling put together and ready to work.

On your workspace…
Create an inspiring work area even if it is your dining table, a little nook in your bedroom or an actual office. Make sure it is both functional and designed to make you WANT to work there.

On setting goals when you’re the boss…
I have to-do lists in so many forms — a Text Edit doc, a notepad, my journal, Teuxdeux — I probably should look into combining everything! The biggest thing that helped me keep myself accountable was when I started diligently tracking my time and how I was spending my days. I had my friend set up an Excel document for me with all these fancy formulas (though I’m sure there is some app out there that helps you do this) and I started tracking how much time I was spending on client work, business development, my blog, taking breaks, etc. The findings were really telling and have helped my structure my day so I can get the most out of it.

On separating work from home…
I’m still working on this one. I’m trying really hard to establish fixed hours for myself and forcing myself to stop. A lot of times I’ll schedule work-outs or social events for the evening so it forces me to get off the computer and stop work for the night. It helps that most of my friends and boyfriend get off work at fixed times, so oftentimes I’ll try to match my schedule to theirs.

On getting the hang of this freelance thing…
I’d say it took me a solid 6-8 months. The process was interesting — a lot of tears, self doubt, mornings I accidentally slept in, all-nighters pulled, days I spent in PJs all day long, days spent entirely doing finances, but I think I finally got the hang of it! I really wish I wasn’t so hard on myself throughout the process. All this stuff takes time and patience is a virtue. I think being a successful freelancer requires a lot of trial and error to figure out what works best for you.

I’d love to know: Do you have any tips for being your own boss, working from home or freelancing in general?

Cheers to all of you! I’m so impressed by freelancers.
I actually have a question for you and other freelancers – how did you know you were ready to take the leap? I’m sure you’ll say you never really know and you just have to go for it, but it seems like one has to reach a certain level of success in a traditional job to even consider it. Or am I wrong? Are there people who started freelancing very early in their careers? I’d love to work for myself eventually, but I am not a huge success in the field I ended up being in, so I’d have no “clients” or guaranteed business if I set out on my own. It looks like I’d have to work for several more years before I could even consider it. I’d love to hear what gave you the confidence or knowledge you were realistically ready to go for it.

For me, freelancing wasn’t so much a matter of choice as it was a necessity. There really isn’t much of a publishing/magazine presence here! If I wanted to continue doing what I do (and I did), I had to go freelance. But I was mentally ready to have a more flexible career, too. I get so bored working on one thing every day and freelancing affords me the change I need to stay interested. Re: breaking out on your own: I would think it’s best to start building your personal portfolio on the side before going at it solo. That’s how I’ve seen it done most often!

I began freelancing very early in my career but at the same time, I am still working part-time on the side for some steady income. For me, styling and designing interiors is something you can run with if you have the talent and love for business. In my opinion, in my field, I don’t believe you have to reach a level of success under another designer to be able to take the leap. I definitely think it’s great to have some good projects under your belt and experience to make sure you are cut out for what services/product you are providing – but if it’s what you truly want in life…I say you just kind of know when you know! :) Good luck to you with all of your endeavors!!

Great post! Happy to see I am not alone. I have found that I feel better when I am dressed casual but comfortable and able to run to a meeting if needed. I like the part about feeling guilty. It happens a lot but really we chose to work from home so we could enjoy a few moments here and there doing EXACTLY what we want! :)

I agree, Bri! First I started by wearing gym clothes. Then I got way over-dressed. Now I’ve found a happy medium that’s comfortable (as you say) but still polished. And I really struggle with those guilty moments! It’s good to know we all go through those emotions.

I found this post very useful, now that I decided to change my career and to be a full-time freelancer. I’m a beginner but my challenges are combining several clients, get actual work done, and do some marketing for myself. I guess it will be easier as time goes by, and I hope the social pressure to show some work gets easier too, because people (friends or family) don’t imagine how much work a freelancer have to do just to get clients, all the work involved in every aspect of being independent! Thank you for this inspiring interviews.

This is SUCH a good post! More than anything it’s nice to know how others deal with the same struggles — it helps to know I’m not the only one feeling guilty about giving in to the occasional TV break :) I think the most important thing I’ve learned is to find what works for me and run with it… after working under “bosses” for years, it’s taken some time to get used to the idea that I’M the only one in charge!

This is was a great blog post. Working from home is a great thing, but it does come with its own struggles. I am blessed to be able to do what I truly love but it really takes a lot of discipline & motivation.

Loved this post! I definitely wondered how I would handle the leap from they-employed to self-employed. Still relatively new to the game, but the things that helped me were: “getting ready for work”, by which I mean, the actual act of getting properly dressed, hair done and face/teeth/etc washed, before sitting down to my desk. It may be a TINY commute, but I needed it to get my mind to transition from home to work. What I still haven’t figured out yet is time management… Because I set my own deadlines – sometimes I have trouble knowing what to prioritize, and I’ll spend a much too long doing something unimportant… Maybe I should look into that excel punchcard idea! http://Www.eatingliterally.typepad.com

This is so spot on and a great read for anyone working from home or wondering how people do it. I started solely freelancing nearly 8 years ago and although I am now paid as an employee, I still creative direct a quarterly magazine from home. The company doesn’t have an office so the entire staff works from home and somehow we manage to produce a 164 page magazine on time four times a year. When I began working from home I struggled a lot and still do with certain things. At first, it was really difficult not to feel lonely or trapped inside the house. Thank god for the company of my dog and the realization that I needed to escape at the end of the day. Taking breaks, running errands, and making lunch dates are absolutely amazing however, this article is correct in that you feel the need to prove to people that you actually do work. For money. No, you can’t always take the afternoon off when your mom or a friend wants to plan a day trip just because you’re home. And the “must be nice” or “I wish I had a job like that” comments do get annoying. After all, they clock out at night so working at night or getting an email about a corrupted file after 5:00 that needs to be corrected and sent immediately, rarely happens to them. As for work attire, I usually check and respond to emails and do any necessary paperwork for a few hours in the morning in my jammies and then take a shower, do my hair and makeup, and dress up and then dive into the creative design part of it. I find it helps make me feel better about myself which translates to my work. If you’re just starting out working from home, don’t worry, you’ll adjust and it will be wonderful. And yes, everyone will be jealous and want you to let their dog out for them. Thanks for the great read!

Totally agree with all your statements, especially about how some people think we can just take afternoons off, like it’s no big deal. There does seem to be this need to prove that, yes, we actually do work! Thanks for all your great input, Kat!

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I'm Archana, and My SoCal'd Life is a travel blog for the adventurous, hungry, and stylish explorer. I moved to San Diego in January 2013 after traveling the world for a year, and love finding, trying, and documenting my travel discoveries—whether that's off-the-beaten-path eats, beautiful beaches, or cool boutiques. >>> Let's go!